JP2018509411A - 塩溶液からフラン−2,5−ジカルボン酸(fdca)を製造する方法 - Google Patents
塩溶液からフラン−2,5−ジカルボン酸(fdca)を製造する方法 Download PDFInfo
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- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims abstract description 220
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000012266 salt solution Substances 0.000 title abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000000243 solution Substances 0.000 claims abstract description 44
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 27
- 238000000926 separation method Methods 0.000 claims abstract description 27
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- 150000001450 anions Chemical class 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000855 fermentation Methods 0.000 claims description 20
- 230000004151 fermentation Effects 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- HIEAIXCEKDTPKU-UHFFFAOYSA-L dipotassium furan-2,5-dicarboxylate Chemical compound [K+].[K+].[O-]C(=O)c1ccc(o1)C([O-])=O HIEAIXCEKDTPKU-UHFFFAOYSA-L 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- MJWAFDPZFACGLR-UHFFFAOYSA-N diazanium furan-2,5-dicarboxylate Chemical compound [NH4+].[NH4+].[O-]C(=O)c1ccc(o1)C([O-])=O MJWAFDPZFACGLR-UHFFFAOYSA-N 0.000 claims description 2
- PMEQUMNFOFODCU-UHFFFAOYSA-L disodium furan-2,5-dicarboxylate Chemical group O1C(=CC=C1C(=O)[O-])C(=O)[O-].[Na+].[Na+] PMEQUMNFOFODCU-UHFFFAOYSA-L 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002028 Biomass Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- -1 polyethylene terephthalic acid Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- RMLWPNGFQAQUNL-UHFFFAOYSA-L O.O.O.O.O1C(=CC=C1C(=O)[O-])C(=O)[O-].[Na+].[Na+] Chemical compound O.O.O.O.O1C(=CC=C1C(=O)[O-])C(=O)[O-].[Na+].[Na+] RMLWPNGFQAQUNL-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical class [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
少なくとも5重量%の濃度を有するMFDCの水性溶液を無機酸(HY)と一緒にして、上記フラン−2,5−ジカルボン酸塩のカチオンと上記無機酸のアニオンとから得られる塩の溶液(MY溶液)中に固体のFDCAを1〜15重量%の濃度で含む反応混合物を形成すること、
固体/液体分離工程において上記反応混合物から固体のFDCAを除去すること、および
上記固体/液体分離工程から得られたMY溶液の一部を、MFDCをHYと一緒にする工程に供給すること
を含む。
5〜30重量%の濃度を有するMFDCの水性溶液を無機酸(HY)と一緒にして、上記フラン−2,5−ジカルボン酸塩のカチオンと上記無機酸のアニオンとから得られる塩の溶液(MY溶液)中に固体のFDCAを1〜15重量%の濃度で含む反応混合物を形成すること、
固体/液体分離工程において上記反応混合物から固体のFDCAを除去すること、および
上記固体/液体分離工程から得られたMY溶液の40〜95重量%を、MFDCをHYと一緒にする工程に供給すること
を含む。
上述した特定の選好がこの方法にも当てはまる。
下記の実験設定が、種々の化合物の既知の溶解度データを使用してコンピュータにおいてモデル化された。
Claims (10)
- フラン−2,5−ジカルボン酸塩(MFDC)をフラン−2,5−ジカルボン酸(FDCA)に転化することによりフラン−2,5−ジカルボン酸(FDCA)を製造する方法であって、下記工程:
少なくとも5重量%の濃度を有するMFDCの水性溶液を無機酸(HY)と一緒にして、上記フラン−2,5−ジカルボン酸塩のカチオンと上記無機酸のアニオンとから得られる塩の溶液(MY溶液)中に固体のFDCAを1〜15重量%の濃度で含む反応混合物を形成すること、
固体/液体分離工程において上記反応混合物から固体のFDCAを除去すること、および
上記固体/液体分離工程から得られたMY溶液の一部を、MFDCをHYと一緒にする工程に供給すること
を含む方法。 - 上記フラン−2,5−ジカルボン酸塩が、フラン−2,5−ジカルボン酸ナトリウム(NaFDC)、フラン−2,5−ジカルボン酸カリウム(KFDC)およびフラン−2,5−ジカルボン酸アンモニウム(NH4FDC)から選択される、請求項1に記載の方法。
- MFDCが、少なくとも10重量%の濃度を有する水性溶液の形態で供給される、請求項1または2に記載の方法。
- 上記無機酸(HY)が、塩酸(HCl)、硝酸(HNO3)および硫酸(H2SO4)から選択される、請求項1〜3のいずれか1項に記載の方法。
- 一緒にされる、MFDCの量およびその含水量、酸の量およびその濃度、ならびにMY溶液の量が、上記反応混合物におけるFDCA濃度が上記反応混合物の総重量に基づいて計算して1〜10重量%、いくつかの実施形態では2〜8重量%、より特に3〜7重量%の範囲であるように選択される、請求項1〜4のいずれか1項に記載の方法。
- 上記固体/液体分離工程から得られたMY溶液の少なくとも40体積%、特に少なくとも50体積%、より特に少なくとも60体積%、いくつかの実施形態では少なくとも70体積%および/または高々95体積%が、MFDCをHYと一緒にする工程に供給される、請求項1〜5のいずれか1項に記載の方法。
- 上記固体/液体分離工程から抜き出されたMY溶液の濃度が、少なくとも5重量%、特に少なくとも10重量%、および/または高々30重量%、好ましくは10〜20重量%である、請求項1〜6のいずれか1項に記載の方法。
- NaFDC、KFDCおよびNH4FDCから選択されるフラン−2,5−ジカルボン酸塩をフラン−2,5−ジカルボン酸(FDCA)に転化することによりフラン−2,5−ジカルボン酸(FDCA)が製造され、下記工程:
5〜30重量%の濃度を有するMFDCの水性溶液を無機酸(HY)と一緒にして、上記フラン−2,5−ジカルボン酸塩のカチオンと上記無機酸のアニオンとから得られる塩の溶液(MY溶液)中に固体のFDCAを1〜15重量%の濃度で含む反応混合物を形成すること、
固体/液体分離工程において上記反応混合物から固体のFDCAを除去すること、および
上記固体/液体分離工程から得られたMY溶液の40〜95重量%を、MFDCをHYと一緒にする工程に供給すること
を含む、請求項1〜7のいずれか1項に記載の方法。 - MFDCが発酵工程から得られたものである、請求項1〜8のいずれか1項に記載の方法。
- 上記固体/液体分離工程から得られたHY溶液の一部が上記一緒にする工程にリサイクルされ、別の部分が上記一緒にする工程にリサイクルされない、請求項1〜9のいずれか1項に記載の方法。
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15159401.7 | 2015-03-17 | ||
EP15159401 | 2015-03-17 | ||
PCT/EP2016/055820 WO2016146753A1 (en) | 2015-03-17 | 2016-03-17 | Method for manufacturing furan-2,5-dicarboxylic acid (fdca) from a salt solution |
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JP2018509411A true JP2018509411A (ja) | 2018-04-05 |
JP6745277B2 JP6745277B2 (ja) | 2020-08-26 |
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JP2017547438A Expired - Fee Related JP6745277B2 (ja) | 2015-03-17 | 2016-03-17 | 塩溶液からフラン−2,5−ジカルボン酸(fdca)を製造する方法 |
JP2017547145A Expired - Fee Related JP6745276B2 (ja) | 2015-03-17 | 2016-03-17 | 固体の塩からフラン−2,5−ジカルボン酸(fdca)を製造する方法 |
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US (2) | US10118908B2 (ja) |
EP (2) | EP3271341A1 (ja) |
JP (2) | JP6745277B2 (ja) |
KR (2) | KR101952060B1 (ja) |
CN (2) | CN107406401B (ja) |
AU (2) | AU2016232141B2 (ja) |
BR (2) | BR112017019642B1 (ja) |
CA (2) | CA2979589C (ja) |
ES (1) | ES2898857T3 (ja) |
MX (2) | MX2017011790A (ja) |
WO (2) | WO2016146752A1 (ja) |
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EP3402787A4 (en) | 2016-01-13 | 2019-11-27 | Stora Enso Oyj | PROCESSES FOR PREPARING 2,5-FURANDICARBOXYLIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF |
AU2018301662B2 (en) | 2017-07-12 | 2022-06-30 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
EP3628667A1 (en) * | 2018-09-28 | 2020-04-01 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Process and salts for the preparation of 2,5-furandicarboxylic acid |
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WO2010143610A1 (ja) * | 2009-06-12 | 2010-12-16 | 日本化薬株式会社 | トリスアゾ化合物からなる色素、インク組成物、記録方法及び着色体 |
CA2777503C (en) | 2009-09-02 | 2018-10-16 | Dsm Ip Assets B.V. | Polypeptides having oxidoreductase activity and their uses |
JP6275038B2 (ja) | 2011-08-16 | 2018-02-07 | ピュラック バイオケム ビー. ブイ. | 発酵ブロス処理にとって有用な、塩化水素酸を用いた沈殿によるカルボン酸のそれらのマグネシウム塩からの回収 |
CN111808053A (zh) * | 2011-08-16 | 2020-10-23 | 普拉克生化公司 | 可用于发酵液处理的通过用盐酸沉淀从羧酸镁盐中回收羧酸的方法 |
CA2859706C (en) | 2011-12-23 | 2020-01-28 | Purac Biochem Bv | Method for isolating a carboxylic acid from an aqueous solution |
CA2863737C (en) * | 2012-02-08 | 2016-11-08 | Purac Biochem B.V. | Carboxylate acidification |
HUE029321T2 (en) * | 2012-04-25 | 2017-02-28 | Purac Biochem Bv | Fermentation process using hydrocyclone |
HUE024575T2 (hu) * | 2012-05-24 | 2016-02-29 | Purac Biochem Bv | Karbonsav kinyerése magnézium-karboxilát elegybõl |
CN102718734A (zh) * | 2012-05-31 | 2012-10-10 | 中国科学技术大学 | 一种4-羟甲基糠酸和2,4-呋喃二甲酸的制备方法 |
NL2011027C2 (en) * | 2013-06-24 | 2014-12-29 | Univ Delft Tech | Process for the preparation of 2,5-furandicarboxylic acid. |
EP2821368A1 (en) * | 2013-07-03 | 2015-01-07 | PURAC Biochem BV | Method for processing magnesium chloride solutions |
CN104059037A (zh) * | 2014-03-25 | 2014-09-24 | 浙江理工大学 | 一种制备2,5-呋喃二甲酸的方法 |
CN103965146B (zh) * | 2014-04-03 | 2016-04-06 | 浙江大学 | 呋喃二甲酸的纯化方法 |
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